Sodium borohydride → HCID 19934850, compound

HRID 1492645Notes

Reaction equation

HRID 1492645 reaction equation
[CH3:1][C:2]1[CH:20]=[C:19]([CH:21]=[O:22])[CH:18]=[C:17]([CH3:23])[C:3]=1[O:4][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].[BH4-].[Na+]>CO>[CH3:1][C:2]1[CH:20]=[C:19]([CH2:21][OH:22])[CH:18]=[C:17]([CH3:23])[C:3]=1[O:4][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18950590Methyl 2-(2,6-dimethyl-4-formylphenoxy)-2-(3-chlorophenyl)acetate

Product 1

HCID 19934850HCID 19934850, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.260 g (3.79 mmol) of the product of Step A in 8 mL methanol was added 0.072 g (1.90 mmol) of sodium borohydride and the reaction mixture was stirred at room temperature for 15 minutes. Excess borohydride was quenched with water, and the reaction mixture was extracted into EtOAc. The organic layer was dried (MgSO4), filtered, evaporated, and then purified on a silica gel flash chromatography column eluted with 30% EtOAc-hexane. The purified fractions were combined, evaporated and dried in vacuo to afford 0.790 g (63%) of the title compound.

Workup

  1. customExcess borohydride was quenched with water
  2. extractionthe reaction mixture was extracted into EtOAc
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified on a silica gel flash chromatography column
  7. washeluted with 30% EtOAc-hexane
  8. customevaporated
  9. customdried in vacuo

Sources & evidence

ORD record
ord-c3747f79d2f642da9692d4d8e3c71bda
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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